Process for



T aryl) burrs STATES PATENT OFFICE PROCESS FOR PREPARING WATER- SOLUBLE CONDENSA'I'ION PRODUCTS Alfred Thauss, Cologne-Deutz, Gustav Mauthe,

Cologne-Holweide, and Arnold Doser, Cologne- Mnlheim, Germany,

assignors, by mesne assignments, to General Aniline Works, 1110., New

York, N. Y.

No Drawing. Application March 11, 1930, Serial No. 435,019, and in Germany March 23, 1929 4 Claims.

The present invention relates to a new process for preparing Water-soluble condensation products from phenolic compounds and halogenated aralkyl compounds containing no hydroxy group.

According to the present invention new condensation products are obtainable by starting from an aromatic hydroxy compound, as for instance phenol, ocand c-naphthol and substitution products thereof, containing no sulfonic acid group and heating the hydroxy compound advantageously in the presence of a catalyst, as for instance, zinc chloride, aluminium chloride, with about the equimolecular quantity of a halogenated aralkyl compound, as for instance 0-, m-, p-,

chloroand bromo-benzylchlorides, diand trichlorobenzylchlorides, xylylchlorides, naphthylchlorides, to a temperature between about 15-l00 C. for about 3-15 hours. The condensation product can be isolated according to known ,methods or it can be sulfonated at a temperature between about 35-80 C. without isolation in the same apparatus by means of oleum, sulfuric acid, chlorosulfonic acid and the like. The sulfuric acid or the alkali metal salts of the condensation product are obtained in the known manner for example by neutralizing with caustic alkali lye and evaporating.

The reaction takes place according to the following equation:

alk=alkylene; Hal=halogen; R: The products thus obtainable are in form of their alkali metal salts weakly colored powders easily soluble in water. They possess in the free form as well as in the form of their alkali metal salts the valuable technical property of preventing animal fibers, such as wool and silk, (to which fibers they may be applied, for instance, in form of their aqueous solution) from absorbing dyestuffs which are dyed in an acid or neutrally reacting bath. Our new products are, therefore, auxiliary substances in dyeing and printing. When applying these new products, for instance, to mixed textile fabrics made of cotton and silk or cotton and wool etc., which are to be printed or dyed, the animal fibers, i. e. the silk or the wool, in the mixed fabrics are prevented. from taking up the dyestufis. In this manner multi-colored efiects are easily obtainable. Our new resists may be applied to the fibers either before or during the dyeing proc- .esses.

The following example will illustrate our invention without limiting it thereto:

Erample:19 parts by weight of phenol, 46 parts by weight of trichlorobenzylchloride obtainable by chlorinating toluene and 0.2 part by weight of Zinc chloride are heated slowly with stirring to 85 C. and when the at first vigorous evolution of hydrogen chloride has subsided the whole is further heated to about 10-l5 C. higher. This temperature is maintained for about 6-8 hours until a test portion becomes viscous on cooling. The temperature is then reduced to 40-45" C. and 28 parts by weight of 20% oleum are dropped in so slowly that the temperature does not exceed C. The internal temperature is then maintained at 65-'70 C. for l-2 hours until a test portion dissolves in water to a clear and colorless solution and remains unchanged on heating.

The working up is carried out in a very simple manner:-

The product is stirred with ice and water, avoiding any strong heating, neutralized with caustic soda lye and evaporated to dryness. The mass can be ground to a colorless powder, which dissolves readily in water to a clear solution and in general, displays a similar behaviour as the product described in the example of application Ser. No. 313,635, filed October 19, 1928 now Patent 1,860,487.

We claim:

1. Process for preparing water-soluble condensation products comprising heating and aromatic hydroxy compound with about the same quantity or" a halogenated aralkylhalogenide containing no hydroxyl group to a temperature of from 15 to 100 C. for 3-15 hours in the presence of a catalyst selected from the group consisting of Zinc chloride and aluminium chloride and sulfonating the condensation product obtained at a temperature between 35 and C.

2. Process for preparing water-soluble condensation products comprising heating phenol with about the same quantity of halogenated benzylchloride to a temperature of from 15 to C. for from 3 to 15 hours in the presence of a catalyst selected from the group consisting of zinc chloride and aluminium chloride and sulfonating the condensation product obtained at a temperature between 35 and 80 C.

3. Process for preparing water-soluble condensation products comprising heating phenol with about the same quantity of trichlorobenzylchloride to a temperature of from 15 to 100 C. for from 3 to 15 hours in the presence of a cataand sulfonating the reaction product at a tem-- perature of between 35 and C. with 28 parts of oleum of 20% strength for from 1 to 2 hours, pouring the mixture into ice and water, neutralizing with a sodium hydroxide solution and evaporating.

ALFRED THAUSS.

GUSTAV MAUTHE.

ARNOLD DOSER. 

